US6528490B2 - Oenothein medicaments - Google Patents
Oenothein medicaments Download PDFInfo
- Publication number
- US6528490B2 US6528490B2 US09/433,977 US43397799A US6528490B2 US 6528490 B2 US6528490 B2 US 6528490B2 US 43397799 A US43397799 A US 43397799A US 6528490 B2 US6528490 B2 US 6528490B2
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- Prior art keywords
- oenothein
- exposure
- mammal
- irritation
- inflammation
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/16—Emollients or protectives, e.g. against radiation
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
Definitions
- the invention is in the field of compositions and methods for treatment of inflammation, irritation and the effects of free radicals, using oenothein ellagitannins.
- Ellagitannins are a diverse family of naturally-occurring compounds consisting of a central core of glucose esterified with hexahydroxydiphenic acid. Ellagitannins are known as active constituents of a variety of medicinal plants (Okuda and Hotano, 1989 , Planta Med . 55(2):117).
- U.S. Pat. No. 5,843,911 issued Dec. 1, 1998 discloses the use of ellagitannins having galloyl and hexahydroxydiphenoyl substituents as hyaluronidase enzyme inhibitors for topical application, to enhance water retention in skin by preventing the hydrolysis of hyaluronic acid.
- the ellagitannins disclosed in U.S. Pat. No. 5,843,911 are identified as “GOD-type” ellagitannins, extractable from a variety of plants.
- U.S. Pat. No. 5,525,594 issued Jun. 11, 1996 discloses the use of the ellagitannin oenothein-B (which is not a “GOD-type” ellagitannin as defined in U.S. Pat. No. 5,843,911) for the treatment of hyperandrogenic disorders by oral, rectal or parenteral administration (also reported in Lesuisse et al., 1996 , J. Nat. Prod . 59(5):490).
- the mechanism of action of oenothein-B is taught to be the inhibition of 5-reductase, an enzyme responsible for the conversion of testosterone to dihydrotestosterone.
- Aqueous extracts of Old World Epilobium angustifolium have been suggested for use as oral anti-inflammatories (German Patent No. 3,605,250 of Jul. 16, 1987), and the active ingredient in such extracts has been identified as the flavonoid compound myricetin glucuronide (3,3′4′,5,5′,7-hexahydroxyflavone-3-O-glucuronide; see Hiermann et al., 1991 , Planta Medica 57:357 and German Patent 3,900,023 of Jul. 12, 1990).
- oenotheins are potent topical anti-inflammatories, anti-irritants and free radical scavengers (useful for treating exposure to free radicals). These activities provide unexpected advantages in topical formulations or medicaments, for example to ameliorate the effects of sunlight on skin. Accordingly, the invention provides formulations comprising an oenothein, including formulations for topical use as free-radical-scavengers or as a prophylactic against damage caused by sunlight or other ionizing radiation, or to treat irritation and inflammation (including irritation and inflammation caused by exposure to sunlight or other agents).
- the oenothein for use in such formulations may for example be oenothein-A or oenothein-B.
- the oenothein may be purified from natural sources, such as plant material, or it may be prepared synthetically.
- compositions Prior to the present invention, there was no motivation to determine the amount of oenothein being administered in herbal remedies, such as Epilobium angustifolium extracts).
- plant extracts for use in such formulations may now be assayed to determine the concentration of oenothein in the extracts so that dosages may be formulated more reliably.
- New World Epilobium angustifolium extracts may be assayed for oenothein-B content.
- Packaging for formulations of the invention may include text that indicates that the formulations are useful for prophylaxis of sunlight induced damage, as free radical scavengers for treating exposure to free radicals, or for treating inflammation or irritation, such text may optionally disclose that the formulations contain an oenothein.
- new plant extracts found to contain an oenothein may be used topically to ameliorate the effects of sunlight, as anti-irritants, as anti-inflammatories, or for treating exposure to free radicals.
- Epilobium spp. other than Epilobium angustifolium may be used for making such extracts where they contain oenothein-A or oenothein-B or mixtures thereof.
- FIG. 1 is a drawing of the known structure of oenothein-A (from Ducrey et al., 1996, supra).
- FIG. 2 is a drawing of the known structure of oenothein-B (from Ducrey et al., 1996, supra).
- FIG. 3 is 500 MHz 1H NMR spectrum for oenothein-B extracted from New World E. angustifolium.
- FIG. 4 is a MALDI negative ion mass spectrum for oenothein-B extracted from New World E. angustifolium.
- FIG. 5 is a LC-MS APCI (negative ion) mass spectrum for oenothein-B extracted from New World E. angustifolium.
- FIG. 6 is a UV-VIS spectrum for oenothein-B extracted from New World E. angustifolium.
- the invention provides formulations or medicaments for treating a variety of symptoms, diseases or disorders, including inflammation and irritation, such as inflammation and irritation of the skin. Inflammation and irritation are characteristic of a wide variety of skin diseases treatable with the compounds of the invention, including psoriasis and eczema.
- the term “irritation” includes conditions medically recognized as pruritus (itching) or prurigo, such as simple or acute pruritis, pruritus ani, pruritus essential, pruritus estivalis, pruritus hiemalis, pruritus senilis, symptomatic pruritus and pruritus vulvae.
- Anti-irritant formulations of the invention accordingly include anitpruritic formulations.
- the term “inflammation” includes conditions medically recognized as dermatitis, including actinic dermatitis, dermatitis aestivalis, allergic dermatitis, atopic dermatitis, berlock dermatitis, dermatitis calorica, cercarial dermatitis, contact dermatitis, cosmetic dermatitis, exfoliative dermatitis, dermatitis herpetiformis, dermatitis hiemalis, infectiosa eczematoides, dermatitis medicamentosa, dermatitis multiformis, dermatitis capillitii, poison ivy dermatitis, primary dermatitis, radiation dermatitis, rhus dermatitis, dermatitis seborrheica, stasis dermatitis, dermatitis venenata, dermatitis verrucosa and x-ray dermatitis.
- the irritation or inflammation treatable using compositions of the invention may accordingly include such conditions as caused by a wide variety of agents, including radiation (such as sunlight and ionizing radiation), chemicals, physical insult (traumatic or prolonged), foreign bodies, electricity, thermic causes (heat or cold) or microorganisms.
- the invention provides methods of medical or cosmetic treatment, in which a therapeutic or prophylactic dose of an oenothein is administered, such as by administration of a pharmacologically acceptable formulation.
- a pharmacologically acceptable formulation may comprise oenothein-B or oenothein-A and a pharmacologically acceptable excipient or carrier, and may comprise a pharmaceutically acceptable salt of the oenothein.
- such formulations may comprise a therapeutically or prophylactically effective amount sufficient to alter, and preferably inhibit, inflammation or irritation, or to quench free radicals.
- pharmaceutically acceptable carrier or “excipient” includes any and all creams, gels, solvents, dispersion media, coatings, antibacterial and antifungal agents, isotonic and absorption delaying agents, and the like that are physiologically compatible and do not significantly adversely effect the pharmaceutical properties (e.g. toxicity and effectiveness) of the oenothein, such as are conventionally used in the cosmetic and pharmaceutical arts.
- the carrier is suitable for topical administration.
- topical administration includes administration to the skin or mucosa, including surfaces of the lung and eye.
- oenotheins may undergo hydrolysis in acid or base, so that pharmaceutically acceptable carriers or excipients may include pH buffers to maintain an acceptable pH for pharmaceutical activity (see Daniel et al., 1991 , J. Natural Products 54(4):946, for a discussion of the effects of pH on ellagitannins).
- a “therapeutically effective amount” refers to an amount effective, at dosages and for periods of time necessary, to achieve the desired therapeutic result, such as reduction or reversal of inflammation or irritation.
- a therapeutically effective amount of an oenothein may vary according to factors such as the disease state, age, sex, and weight of the individual, and the ability of the oenothein to elicit a desired response in the individual. Dosage regimens may be adjusted to provide the optimum therapeutic response.
- a therapeutically effective amount is also one in which any toxic or detrimental effects of the oenothein are outweighed by the therapeutically beneficial effects.
- a “prophylactically effective amount” refers to an amount effective, at dosages and for periods of time necessary, to achieve the desired prophylactic result, such as preventing or inhibiting the rate of inflammation or irritation or the onset of inflammation or irritation, or quenching of free radicals.
- a prophylactically effective amount can be determined as described above for the therapeutically effective amount.
- a preferred range for therapeutically or prophylactically effective amounts of an oenothein may be 0.1% to 10% by weight.
- One method of cosmetic, prophylactic or therapeutic treatment is to apply an oenothein topically to the area of inflammation or irritation. Dosage values may vary with the severity of the condition to be alleviated. It is to be further understood that for any particular subject, specific dosage regimens may be adjusted over time according to the individual need and the judgement of the person administering or supervising the administration of the compositions, and that dosage ranges set forth herein are exemplary only and are not intended to limit the scope or practice of the methods of the invention.
- compositions of the present invention comprising an oenothein
- containers having labels that provide instructions for use of the formulation to: treat inflammation, treat irritation, scavenge free radicals, or ameliorate the effects of exposure to sunlight.
- the labels may also disclose that the compositions comprise an oenothein.
- the present invention provides formulations for treating inflammation or irritation that are prepared from purified oenothein-B obtained from Epilobium angustifolium , where the oenothein-B is purified to a concentration of greater than 9.6% prior to formulation.
- purified oenothein-B from Epilobium angustifolium may be utilized in the present invention in concentrations ranging from 9.6% up to concentrations of approximately 100%.
- a variety of methods may be used to purify oenotheins from natural sources for use in the various aspects of the present invention.
- U.S. Pat. No. 5,525,594 (incorporated herein by reference) discloses methods of preparing oenothein-B from plants.
- Ducrey et al., 1996, supra disclose oenothein-A and oenothein-B purification and characterization methods (incorporated herein by reference).
- Alternative purification methods may be used in accordance with the present invention, provided that they may be used to produce a pharmaceutically acceptable preparation of purified oenothein-B suitable for use in the various aspects of the present invention.
- a purified aqueous extract was obtained from New World Epilobium angustifolium (Canadian Willowherb) and subjected to a variety of analytical techniques, which unambiguously identify the purified compound as oenothein-B.
- This analysis included mass spectroscopy and nuclear magnetic resonance spectrometry, as shown in FIGS. 3 through 6. While oenothein-B was found by these methods to be present in solvent-free aqueous extracts of Canadian Willowherb at levels up to 9.6%, myricetin glucuronide—the substance identified as the active ingredient of the anti-inflammatory action of Old World Epilobium angustifolium (see the Background section herein)—was not found in extracts of Canadian Willowherb.
- This example shows the effectiveness of the purified oenothein-B characterized in Example 1 in treating inflammation and irritation.
- an oenothein-B extract from Canadian Willowherb formulated in a lotion ameliorated the irritant effects of 15% lactic acid, as measured after 0.5, 1, 4 and 24 hours, compared to controls with no treatment, treatment with water and treatment with the lotion alone (containing no extract).
- This example shows the free radical scavenging activity of oenothein-B.
- a sample of the oenothein-B extract from Canadian Willowherb described in Example 1 was assessed using the xanthine oxidase/acetaldehyde spectrophotometric method, in which superoxide radical ions are generated in vitro using acetaldehyde and xanthineoxidase, in the presence of test compounds (Fridovich, 1970 , Journal of Biological Chemistry 245:4053; Hodgson and Fridovich, 1976 , Biochimica et Biophysica Acta 430:182).
- the scavenging of free superoxide radicals is quantitated spectrometrically and expressed in terms of percentage of radicals scavenged. Assays were performed with 1% (w/v) and 0.1% (w/v) dilutions of the dried extract, which yielded up to 100% scavenging activity and up to 99% scavenging activity respectively.
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Toxicology (AREA)
- Molecular Biology (AREA)
- Epidemiology (AREA)
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Abstract
Description
Claims (24)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA2282185 | 1999-09-10 | ||
CA002282185A CA2282185A1 (en) | 1999-09-10 | 1999-09-10 | Oenothein medicaments |
Publications (2)
Publication Number | Publication Date |
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US20030004131A1 US20030004131A1 (en) | 2003-01-02 |
US6528490B2 true US6528490B2 (en) | 2003-03-04 |
Family
ID=4164135
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US09/433,977 Expired - Lifetime US6528490B2 (en) | 1999-09-10 | 1999-11-04 | Oenothein medicaments |
Country Status (4)
Country | Link |
---|---|
US (1) | US6528490B2 (en) |
AU (1) | AU1645700A (en) |
CA (1) | CA2282185A1 (en) |
WO (1) | WO2001019377A1 (en) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20100303854A1 (en) * | 2009-04-27 | 2010-12-02 | Mary Kay Inc. | Botanical anti-acne formulations |
WO2015024128A1 (en) | 2013-08-22 | 2015-02-26 | Lucas Meyer Cosmetics Canada Inc. | Anti-dandruff compositions, and methods of use thereof |
US9138401B2 (en) | 2011-12-19 | 2015-09-22 | Mary Kay Inc. | Combination of plant extracts to improve skin tone |
US20180256619A1 (en) * | 2017-03-09 | 2018-09-13 | Epilobium, Inc. | Methods of use for oenothein a and b from epilobium species |
US10500152B2 (en) | 2014-03-10 | 2019-12-10 | Mary Kay Inc. | Skin lightening compositions |
IT202000014011A1 (en) | 2020-06-11 | 2021-12-11 | St Farmochimico Fitoterapico Epo S R L Ed In Forma Abbreviata Epo S R L | PROCESS OF PREPARATION OF AN EXTRACT OF EPILOBIUM SPP. WITH HIGH ENOTEIN B CONTENT |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP3940633B2 (en) * | 2002-05-28 | 2007-07-04 | 株式会社ノエビア | Topical skin preparation |
WO2004016236A1 (en) * | 2002-08-14 | 2004-02-26 | Fancl Corporation | Cosmetics |
JP2011182703A (en) * | 2010-03-08 | 2011-09-22 | Asahi Group Holdings Ltd | Food and drink including 1, 2-di-o-galloyl-4,6-hhdp-b-d-glucopyranose at high concentration |
JP6355129B2 (en) * | 2014-11-06 | 2018-07-11 | 国立研究開発法人農業・食品産業技術総合研究機構 | Food / beverage products containing 1,2-di-O-galloyl-4,6-HHDP-bd-glucopyranose in high concentration |
KR102376806B1 (en) * | 2020-03-05 | 2022-03-21 | 주식회사 메타이뮨텍 | Compositions for reducing weight comprising Oenothein B analogs as effective component |
Citations (12)
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JPS5838209A (en) | 1981-08-29 | 1983-03-05 | Sunstar Inc | Tannin-containing composition for skin for external application |
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FR2712495A1 (en) * | 1993-11-16 | 1995-05-24 | Roussel Uclaf | Application of Óoenotheine B to obtain a medicament intended for the treatment of disorders linked to hyperandrogenism, and the pharmaceutical compositions containing it. |
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Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
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HU222049B1 (en) * | 1996-12-16 | 2003-04-28 | Qms Consulting Bt | Pharmaceutical composition for decreasing prostata inflammation and bph (beningus prostata hyperplasia) comprising plant component parts |
-
1999
- 1999-09-10 CA CA002282185A patent/CA2282185A1/en not_active Abandoned
- 1999-11-04 US US09/433,977 patent/US6528490B2/en not_active Expired - Lifetime
- 1999-12-01 AU AU16457/00A patent/AU1645700A/en not_active Abandoned
- 1999-12-01 WO PCT/CA1999/001155 patent/WO2001019377A1/en active Application Filing
Patent Citations (13)
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US5073545A (en) | 1987-06-09 | 1991-12-17 | Lion Corporation | Agent containing an ellagic acid series compound for external application and use thereof |
DE3900023A1 (en) | 1989-01-02 | 1990-07-12 | Plantamed Arzneimittel Gmbh | MYRICETIN-3-O-SS-D-GLUCURONIDE |
US5466452A (en) | 1991-02-28 | 1995-11-14 | Phytopharm Ltd. | Pharmaceutical compositions for the treatment of skin disorders |
US5198217A (en) | 1991-09-24 | 1993-03-30 | Choice Pharmaceuticals | Topical demulcent for viral and inflammatory diseases of the skin |
FR2712495A1 (en) * | 1993-11-16 | 1995-05-24 | Roussel Uclaf | Application of Óoenotheine B to obtain a medicament intended for the treatment of disorders linked to hyperandrogenism, and the pharmaceutical compositions containing it. |
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US5843987A (en) | 1996-10-31 | 1998-12-01 | The Procter & Gamble Company | Method of stimulating gastrointestinal motility with ellagic acid |
US5804168A (en) | 1997-01-29 | 1998-09-08 | Murad; Howard | Pharmaceutical compositions and methods for protecting and treating sun damaged skin |
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Cited By (19)
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US8440237B2 (en) | 2009-04-27 | 2013-05-14 | Mary Kay Inc. | Botanical anti-acne formulations |
US8481090B2 (en) | 2009-04-27 | 2013-07-09 | Mary Kay Inc. | Botanical formulations |
US8747926B2 (en) | 2009-04-27 | 2014-06-10 | Mary Kay Inc. | Botanical formulations |
US20100303854A1 (en) * | 2009-04-27 | 2010-12-02 | Mary Kay Inc. | Botanical anti-acne formulations |
US9561198B2 (en) | 2009-04-27 | 2017-02-07 | Mary Kay Inc. | Botanical formulations |
US11638735B2 (en) | 2009-04-27 | 2023-05-02 | Mary Kay Inc. | Botanical formulations |
US10953058B2 (en) * | 2009-04-27 | 2021-03-23 | Mary Kay Inc. | Botanical formulations |
US10682381B2 (en) | 2009-04-27 | 2020-06-16 | Mary Kay Inc. | Botanical formulations |
US10780041B2 (en) | 2011-12-19 | 2020-09-22 | Mary Kay Inc. | Combination of plant extracts to improve skin tone |
US9138401B2 (en) | 2011-12-19 | 2015-09-22 | Mary Kay Inc. | Combination of plant extracts to improve skin tone |
US9861573B2 (en) | 2011-12-19 | 2018-01-09 | Mary Kay Inc. | Combination of plant extracts to improve skin tone |
US11865202B2 (en) | 2011-12-19 | 2024-01-09 | Mary Kay Inc. | Combination of plant extracts to improve skin tone |
WO2015024128A1 (en) | 2013-08-22 | 2015-02-26 | Lucas Meyer Cosmetics Canada Inc. | Anti-dandruff compositions, and methods of use thereof |
US10004678B2 (en) | 2013-08-22 | 2018-06-26 | Lucas Meyer Cosmetics Canada Inc. | Anti-dandruff compositions, and methods of use thereof |
US10500152B2 (en) | 2014-03-10 | 2019-12-10 | Mary Kay Inc. | Skin lightening compositions |
US11123356B2 (en) * | 2017-03-09 | 2021-09-21 | Epilobium, Inc. | Methods of use for oenothein A and B from Epilobium species |
US20180256619A1 (en) * | 2017-03-09 | 2018-09-13 | Epilobium, Inc. | Methods of use for oenothein a and b from epilobium species |
IT202000014011A1 (en) | 2020-06-11 | 2021-12-11 | St Farmochimico Fitoterapico Epo S R L Ed In Forma Abbreviata Epo S R L | PROCESS OF PREPARATION OF AN EXTRACT OF EPILOBIUM SPP. WITH HIGH ENOTEIN B CONTENT |
WO2021250110A1 (en) | 2020-06-11 | 2021-12-16 | Istituto Farmochimico Fitoterapico Epo S.R.L. Ed In Forma Abbreviata: Epo S.R.L. | Process for the preparation of an extract of epilobium spp. with high oenothein b content |
Also Published As
Publication number | Publication date |
---|---|
US20030004131A1 (en) | 2003-01-02 |
CA2282185A1 (en) | 2001-03-10 |
WO2001019377A1 (en) | 2001-03-22 |
AU1645700A (en) | 2001-04-17 |
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